ДАНСИЛКАДАВЕРИН ДИДАНСИЛКАДАВЕРИН

Description

Dansylcadaverine didansylcadaverine is a bis-dansyl derivative of cadaverine (pentane-1,5-diamine), in which both amino groups of the diamine are linked to a dansyl (5-dimethylaminonaphthalene-1-sulfonyl) fluorescent label. Crystalline substance, synonyms: didansylcadaverine crystalline, didansylcadaverine, pentane-1,5-bis(dimethylaminonaphthalenesulfonamide), N,N'-(1,5-Pentanediyl)bis[5-(dimethylamino)-1-naphthalenesulfonamide].

Basic Attributes

• CAS No: 55521-24-9
• Chemical formula: C29H36N4O4S2
• Molecular weight: 568.75
• Exact weight: 568.218
• DSSTox ID: DTXSID30204094
• PSA Specifications: 116
• XLogP3: 5.4

Physico-chemical characteristics

For CAS 55521-24-9, only molecular and exact mass, calculated PSA and XLogP3 are given in open reference sources. Data on density, melting point, boiling point, flash point, refractive index, solubility and vapor pressure have not been published.

Structure and relationship with monodansyl analogue

The compound is structurally related to monodansylcadaverine (dansylcadaverine), a widely used fluorescent probe for labeling autophagic vacuoles and a high-affinity substrate for transglutaminases. The bis-dansyl (double) form contains two fluorophores on one diamine molecule, which distinguishes it from its monosubstituted analogue in molecular weight and spectral properties.

Safety Information

WGK Germany: 3 (hazard class for the aquatic environment according to the German classification). No other GHS classifications, H- and P-phrases, or transport codes for this CAS number were found in open sources.

Scope of application

It is used as a fluorescent reagent of the dansyl series in biochemical studies related to the labeling of diamines and the study of enzymes that work with polyamines (in particular, transglutaminases), by analogy with the known activity of monodansylcadaverine. Reagent for research purposes only.

Storage and transportation

Store at a temperature of 2–8 °C (storage conditions specified by the manufacturer), in an airtight container, protected from light. Wear gloves and safety glasses when working in a fume hood.

Implications for the biochemistry of polyamines

Cadaverine (pentane-1,5-diamine) is a biogenic polyamine, a product of lysine decarboxylation; its dansyl derivatives are used as markers in the study of polyamine metabolism, the activity of transglutaminases (enzymes that catalyze the formation of covalent cross-links between proteins through side amino groups) and the processes of cellular autophagy, where the monodansylated analogue serves as a classical fluorescent probe for visualizing autophagic vacuoles. Double dansylation in this compound potentially allows the study of bivalent interactions of the molecule with two independent binding sites of an enzyme or target protein simultaneously.

Analytical identification

Authenticity is confirmed by spectral methods (NMR, mass spectrometry) based on the formula C29H36N4O4S2, molecular weight 568.75 and exact mass 568.218.